


Double Your Pleasure

by Wolves_of_Innistrad



Series: Tumblr Teen Wolf ficlets [6]
Category: Teen Wolf (TV)
Genre: Based on a Tumblr Post, Bottom!Stiles, Derek is resourceful, Double Dildo, Hands Free Orgasm, M/M, Prostate Orgasm, Simultaneous Orgasm, Smut, Stiles is above age, ambigously canon compliant, bottom!Derek, near - Freeform, sterek, two bottoms no waiting
Language: English
Status: Completed
Published: 2013-10-18
Updated: 2013-10-18
Packaged: 2017-12-29 18:32:06
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 1,527
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1008646
Author URL: https://archiveofourown.org/users/Wolves_of_Innistrad/pseuds/Wolves_of_Innistrad
Summary: <blockquote class="userstuff">
              <p>Inspired by this post.  http://colethewolf.tumblr.com/post/64353324867/maybe-derek-and-stiles-can-ride-one-of-those-two-side</p>
<p>Derek and Stiles finally are together, but how will they stay together when they discover they're both bottoms?  Derek thinks he has an idea...</p>
            </blockquote>





	Double Your Pleasure

       "Derek..."  Stiles says apprehensively, following his newly official boyfriend into the bedroom.  “We still need to talk about, well, what we discussed last night.”

      “Huh?” Derek barely answers, busying pulling a large, non-descript bag from his closet and inspecting the contents.

      “About how we’re both, you know?  _Bottoms?”_   Stiles continues, gesticulating wildly with his arms.  He strips off his worn red hoodie, tight biceps briefly flexing as he throws it into the corner.  “I really like you.  Like, _really_ like you, but how is this going to work?  I mean, do we just take turns topping?  I guess that isn’t so bad, but it might be a bit, I don’t know, unfulfilling?”

      Derek has busied himself looking through the items in the bag, slowly pulling them out one by one.  As Stiles moves closer, eyes just barely unable to peer inside, he notices what Derek has removed from the bag and placed on the bed.  Two bottles of lube, two matching, medium sized dildos, and a few boxes of condoms in assorted sizes and flavors.

      The blood rushes to Stiles’ face as he gets an idea of what they’re going to do.  “So, uh, I guess topping with a dildo in my ass is a thing that’s in my immediate future, huh?”  he mumbles nervously, hands reaching up to clasp his neck and rub at the nape.

      Picking up the final item in the bag, Derek places it next to the now emptied contents, a small smirk spreading on his face.  “Well, I had _actually_ planned on saving that for later,” Derek begins, turning to give Stiles a mischievous smile.  “I bought a little something that should help us both out.”

      As Derek pats the package, Stiles’ mind begins to race, trying to figure out how Derek could have solved the problem.  Eventually, it settles on the only logical answer, and the same devilish smile parts Stiles’ own lips.  “You didn’t Derek, tell me you didn’t,” Stiles squeals, near giddy with excitement.  He reaches for the package, but Derek rebuffs him, holding out a strong hand to his chest.

      “Get undressed and go prep yourself in the bathroom down the hall,” Derek commands, already pulling at the hem of his Henley, shucking it in one practiced motion.

      Stiles wastes no time in doffing his clothes and rushing to the bathroom.  When he returns, he finds Derek in the bed, naked and already fingering himself open.  The sight stops him short, clutching to the jamb to stay upright.

       _“Jeez Derek!”_ Stiles exhales, flush spreading down his body as his limp dick begins twitching to life.  “Warn a guy next time.  Don’t want me coming before we even get to try out our new toy.”

      “Well, since I’ve been doing most of the topping before our relationship officially began and I felt comfortable to tell you how much I wanted to be on the receiving end,” Derek starts, one hand cradling his head while the other scissors his opening, “I though it only fair I get first go.”

      Stiles doesn’t wait for an invitation, jumping on the bed and immediately engulfing Derek’s sizeable manhood in his warm mouth.  A few sucks later and he has the older man moaning out his name in between gasps, Stiles’ lithe fingers having adroitly switched places with Derek’s own.  He leans up to capture Derek’s lips in a kiss before glancing at the package. 

      “Can I?” Stiles asks, as if it was his birthday and this was the present he’d been waiting all year for.

      “Go right ahead,” Derek huffs out, body squirming under Stiles.

      Soon the brown bag has been discarded, leaving only a shiny, black, double-ended dildo lying on the bed.  Stiles’ eyes go wide, taking in the impressive length and girth of it.  He’d heard about them before, but, being a strict bottom, never figured he’d have much use for one.  Until now that is.

      “F-fuck, just, Stiles get it in me.  _Now!_ ”  Derek groans, needy and desperate.  He hates being that way, but also revels in it.  Stiles is, so far, the only person who knows how much he wants to take it.  The depths of his desire for a cock to fill him to bursting and fuck him until he walks funny for a week.

      Stiles obediently lathers it up, easily slipping the head inside Derek before meeting any resistance.  With about a quarter of it in his lover, Derek raises a hand, motions for him to stop.

      “Wait, gotta, gotta get you ready,” he moans, fumbling towards Stiles' general direction.

      Stiles scoots over before allowing Derek to manhandle him into position, sitting on Derek’s face.  The hot breath on his hole alerts him to Derek’s intention before the cool wetness of the older man’s tongue begins probing him.  Derek lathes at his rosebud, slowly working a finger in along with his tongue, producing gasps of rapturous delight from Stiles.

      “Oh _fuck_ , Derek,” Stiles whimpers, legs already shaking from pleasure.  While Derek continues rimming him, he leisurely gives the older man head and toys with his hole, working the dildo in and out, but never going past the allotted length Derek specified.  “Shit, I think I’m ready.”

      At that, Derek pushes him off and moves to align himself in the middle of the headboard of the king size bed.  Beckoning Stiles down, Derek grabs the lube and slicks the other end of the dildo and reapplies some to his own end.  Stiles positions himself at Derek’s feet, trying to work out the logistics of how they are going to do this. 

      “Just lay back and help me feed it to you, it’ll all work out eventually,” Derek assures him, biting down on his lip to suppress a moan.

      Doing as instructed, Stiles lay on his back and scoots down until he can feel the dildo prodding at his entrance.  Their legs are mirrored, each with one on top of and the other under, the other’s.  True to his word, Derek begins working the dildo into Stiles’ ass, eliciting a slight whimper from the younger man.  When Stiles has taken the same amount as Derek has, the older man speaks.

      “Ok, now, we both need to push towards each other until our asses touch.  That way we’ll know we’ve taken it all,” Derek instructs them, already beginning his descent.  A low rumble emanates from Derek’s chest as he impales himself; followed closely by a long hiss from Stiles who takes the full length like a champ.

      “F-fuck,” Stiles breathes, feeling fuller than he’s ever felt, aside from Derek being inside him. 

      “I know, it’s, fuck, it’s amazing, right?” Derek questions, slowly rocking his hips.

      Stiles’ reply dies in his throat as Derek rocks into him.  Instead, a loud, low moan escapes him.  Learning quickly, he repeats the motion, prompting the same response from his lover.  After a few moments, the pair works out a steady rhythm, undulating and swiveling their hips to slowly fuck each other using only the dildo.

      “Shit, it’s like, it’s like fucking and being fucked at the same time,”  Stiles exclaims between thrusts.

      “Why weren’t we doing this from the beginning?” Derek asks, dazed.  He tries something new, rocking downwards, causing the dildo to thrust up into Stiles.  A slight yelping noise followed by a greedy moan tells him it had the intended effect.

      “F-fucker!”  Stiles laughs, mirroring the motion, causing Derek to arch his back and growl in delight.

      Soon, the entire room is filled with only the moans and frenzied panting of the two men as they work themselves closer and closer to climax.  Both their dicks are drooling excessive amounts of precum, much of it dripping down onto the double-sided dildo they are currently using to fuck each other senseless.  Neither man devotes any time to their engorged cocks, hands only rubbing at the legs of their partner as they focus all their attention on their connected asses and prostates. 

      Derek is the first to come, screaming Stiles’ name and bucking wildly.  The added friction drives Stiles over the edge, fusing their orgasms as they ride it out together.

      Coming down from the extreme high, the two share in the post-orgasmic bliss, not even bothering to remove their new toy from between them.  Horny bastards that they both are, little thrusts and teasing pushes linger for a few minutes before both grow tired and move to clean themselves up.

      “Well,” Stiles begins, face looking flush and freshly fucked, “That was certainly a solution to our problem.”

      “Sure was,” Derek responds lazily, wiping them both down with a damp cloth.  “By the way, you need to make sure you shave before next Friday.  You know, _down there_.”

      “Uh, why?” Stiles inquires, puzzled.

      “I’m having molds of our dicks made so we can have a double-dildo with our own cocks on either end,” Derek replies nonchalantly.  He smacks Stiles’ ass as the younger man rolls over and begins laughing.

      “Ok, never mind, _that’s_ the best solution to our problem,” Stiles admits, pulling his boyfriend down for a passionate kiss.  Maybe having another bottom for a boyfriend won’t be so bad after all he thinks. 


End file.
